In vitro enzymatic oxidation of a fluorine-tagged sulfido substrate analogue: a 19F NMR investigation |
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| Authors: | Tremblay Amy E Buist Peter H Hodgson Derek Dawson Brian Whittle Ed Shanklin John |
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| Institution: | Department of Chemistry, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, Canada K1S 5B6. |
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| Abstract: | 1H-decoupled 19F NMR has been used to monitor the highly regioselective oxidation of a fluorine-tagged thia-fatty acid derivative by castor stearoyl-ACP delta9 desaturase. The major enzymatic product, after reductive work-up, was identified as 9-fluoro-1-nonanol. This compound could be easily distinguished from substrate and a 9-sulfoxy by-product on the basis of its 19F NMR chemical shift and spiking experiments using authentic standards. Structural assignment of the cleavage product was confirmed by GC-MS analysis of the enzymatic products. |
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| Keywords: | NMR 19F substituent effects oxidation desaturase |
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